Triethylamine → HCID 57682963, compound

HRID 494311Notes

Reaction equation

HRID 494311 reaction equation
[CH:1]([O:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][C@H:9]([C:13](O)=[O:14])[CH2:8]1)=[O:6])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O>C1COCC1>[OH:14][CH2:13][C@H:9]1[CH2:10][CH2:11][CH2:12][C@@H:7]([C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 57682965HCID 57682965, compound

Product 1

HCID 57682963HCID 57682963, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

140 g of (1S,3R)-3-isopropoxycarbonylcyclohexanecarboxylic acid are dissolved in THF, and 100 ml of triethylamine was added. At −10° C., 68.4 ml of ethyl chloroformate were added dropwise, and the suspension was stirred overnight. After filtration through celite, 55 g of sodium borohydride are added at 0° C., and the suspension is stirred at RT for a further 6 h. A further 25 g of sodium borohydride are added, and the suspension is stirred overnight. Water is added and the solution was stirred for 2 h. The phases are separated and the aqueous phase is extracted with MTBE, and the combined organic phases were washed with sat. NaCl solution, dried over MgSO4 and concentrated. 105 g of isopropyl (1R,3S)-3-hydroxymethylcyclohexanecarboxylate were obtained as a colorless oil.

Workup

  1. filtrationAfter filtration through celite, 55 g of sodium borohydride
  2. additionare added at 0° C.
  3. stirringthe suspension is stirred at RT for a further 6 h
  4. additionA further 25 g of sodium borohydride are added
  5. stirringthe suspension is stirred overnight
  6. additionWater is added
  7. stirringthe solution was stirred for 2 h
  8. customThe phases are separated
  9. extractionthe aqueous phase is extracted with MTBE
  10. washthe combined organic phases were washed with sat. NaCl solution
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-c4a80989496f4c90a6b2c1ca8661c83c
Source dataset
uspto-grants-2009_05
Patent number
US07538131B2

Reaction notes

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